3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (BioDeep_00000027572)

   

human metabolite Endogenous


代谢物信息卡片


(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid

化学式: C9H16O9 (268.0794286)
中文名称:
谱图信息: 最多检出来源 Mus musculus(not specific) 8.09%

分子结构信息

SMILES: C(C(C(C(C(C(CO)O)O)O)O)O)C(=O)C(=O)O
InChI: InChI=1S/C9H16O9/c10-2-5(13)7(15)8(16)6(14)3(11)1-4(12)9(17)18/h3,5-8,10-11,13-16H,1-2H2,(H,17,18)/t3-,5-,6+,7+,8+/m0/s1

描述信息

3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855) [HMDB]
3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855).

同义名列表

20 个代谢物同义名

(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid; (4S,5R,6R,7R,8S)-4,5,6,7,8,9-Hexahydroxy-2-oxononanoate; 2-Keto-3-deoxy-D-glycero-D-galacto-NONONic acid; 2-oxo-3-Deoxy-D-glycero-galactononulosonic acid; 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid; 3-Deoxyglycerogalacto-2-nonulopyranosonic acid; 3-Deoxy-D-glycero-D-galacto-nonulosonic acid; 2-oxo-3-Deoxy-D-glycero-galactononulosonate; 2-Keto-3-deoxy-D-glycero-D-galacto-NONONate; 3-Deoxyglycerogalacto-2-nonulopyranosonate; 3-Deoxy-D-glycero-D-galacto-2-nonulosonate; 3-Deoxy-D-glycero-D-galacto-nonulosonate; 3-Deoxyglycero-galacto-nonulosonic acid; 3-Deoxyglycero-galacto-nonulosonate; Sialosonic acid; Sialosonate; Deoxy-KDN; 2-KDN; SiaX; KDN



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Yang Liu, Guo-Yun Chen, Pan Zheng. Sialoside-based pattern recognitions discriminating infections from tissue injuries. Current opinion in immunology. 2011 Feb; 23(1):41-5. doi: 10.1016/j.coi.2010.10.004. [PMID: 21208791]
  • Shinji Go, Chihiro Sato, Kimio Furuhata, Ken Kitajima. Oral ingestion of mannose alters the expression level of deaminoneuraminic acid (KDN) in mouse organs. Glycoconjugate journal. 2006 Jul; 23(5-6):411-21. doi: 10.1007/s10719-006-6734-z. [PMID: 16897182]
  • Fredoen Valianpour, Nicolaas G G M Abeling, Marinus Duran, Jan G M Huijmans, Willem Kulik. Quantification of free sialic acid in urine by HPLC-electrospray tandem mass spectrometry: a tool for the diagnosis of sialic acid storage disease. Clinical chemistry. 2004 Feb; 50(2):403-9. doi: 10.1373/clinchem.2003.027169. [PMID: 14684624]
  • Karthik Viswanathan, Shawn Lawrence, Stephan Hinderlich, Kevin J Yarema, Yuan C Lee, Michael J Betenbaugh. Engineering sialic acid synthetic ability into insect cells: identifying metabolic bottlenecks and devising strategies to overcome them. Biochemistry. 2003 Dec; 42(51):15215-25. doi: 10.1021/bi034994s. [PMID: 14690432]
  • Alexander S Shashkov, Larisa N Kosmachevskaya, Galina M Streshinskaya, Lyudmila I Evtushenko, Olga V Bueva, Viktor A Denisenko, Irina B Naumova, Erko Stackebrandt. A polymer with a backbone of 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid, a teichuronic acid, and a beta-glucosylated ribitol teichoic acid in the cell wall of plant pathogenic Streptomyces sp. VKM Ac-2124. European journal of biochemistry. 2002 Dec; 269(24):6020-5. doi: 10.1046/j.1432-1033.2002.03274.x. [PMID: 12473097]
  • T Angata, D Nakata, T Matsuda, K Kitajima, F A Troy. Biosynthesis of KDN (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid). Identification and characterization of a KDN-9-phosphate synthetase activity from trout testis. The Journal of biological chemistry. 1999 Aug; 274(33):22949-56. doi: 10.1074/jbc.274.33.22949. [PMID: 10438460]
  • T Angata, D Nakata, T Matsuda, K Kitajima. Elevated expression of free deaminoneuraminic acid in mammalian cells cultured in mannose-rich media. Biochemical and biophysical research communications. 1999 Aug; 261(2):326-31. doi: 10.1006/bbrc.1999.1033. [PMID: 10425185]
  • B Guhl, M Ziak, J Roth. Unconventional antigen retrieval for carbohydrate and protein antigens. Histochemistry and cell biology. 1998 Dec; 110(6):603-11. doi: 10.1007/s004180050323. [PMID: 9860259]
  • T Angata, K Kitajima, S Inoue, J Chang, T G Warner, F A Troy, Y Inoue. Identification, developmental expression and tissue distribution of deaminoneuraminate hydrolase (KDNase) activity in rainbow trout. Glycobiology. 1994 Aug; 4(4):517-23. doi: 10.1093/glycob/4.4.517. [PMID: 7827413]